Design, Synthesis, and Self-Assembly Behavior of Liquid-Crystalline Bis-[60]Fullerodendrimers

Bis-[60]fullerodendrimers were synthesized by assembling [60]fullerene-containing type I (terminal olefin) and type II (α,β-unsaturated carbonyl olefin) olefins through the olefin cross-metathesis reaction. The synthetic modular approach developed in this study allowed the preparation of mono-[60]fullerodendrimers and their [60]fullerene-free analogues. First- and second-generation poly(aryl ester) dendrons carrying cyanobiphenyl mesogens were used as liquid-crystalline promoters. The liquid-crystalline properties were studied by polarized optical microscopy, differential scanning calorimetry, and small-angle X-ray scattering. In agreement with the nature and structure of the dendrimers, nematic, smectic, and multisegregated lamellar phases were observed. Owing to its versatility and tolerance towards many functional groups, olefin cross-metathesis proved to be a reaction of choice for the elaboration of molecular materials with complex architectures.